PL119196B1 - Method of manufacture of nitriles of fatty acids and glycerol from glycenides,especially from natural fats and oilsiz gliceridov,glavnym obrazom iz natural'nykh zhirov i masel - Google Patents
Method of manufacture of nitriles of fatty acids and glycerol from glycenides,especially from natural fats and oilsiz gliceridov,glavnym obrazom iz natural'nykh zhirov i masel Download PDFInfo
- Publication number
- PL119196B1 PL119196B1 PL1978209133A PL20913378A PL119196B1 PL 119196 B1 PL119196 B1 PL 119196B1 PL 1978209133 A PL1978209133 A PL 1978209133A PL 20913378 A PL20913378 A PL 20913378A PL 119196 B1 PL119196 B1 PL 119196B1
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- Prior art keywords
- reaction
- fatty acid
- temperature
- phase
- glycerin
- Prior art date
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims description 134
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 96
- 239000000194 fatty acid Substances 0.000 title claims description 96
- 229930195729 fatty acid Natural products 0.000 title claims description 96
- 238000000034 method Methods 0.000 title claims description 54
- 239000003925 fat Substances 0.000 title claims description 52
- 150000004665 fatty acids Chemical class 0.000 title claims description 42
- 150000002825 nitriles Chemical class 0.000 title description 27
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000006243 chemical reaction Methods 0.000 claims description 95
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 85
- -1 fatty acid nitriles Chemical class 0.000 claims description 68
- 235000011187 glycerol Nutrition 0.000 claims description 63
- 239000003054 catalyst Substances 0.000 claims description 44
- 229910021529 ammonia Inorganic materials 0.000 claims description 36
- 125000005456 glyceride group Chemical group 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 26
- 239000012071 phase Substances 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000005194 fractionation Methods 0.000 claims description 10
- 239000003921 oil Substances 0.000 claims description 10
- 238000005191 phase separation Methods 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 229910052725 zinc Inorganic materials 0.000 claims description 9
- 239000011701 zinc Substances 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 239000007791 liquid phase Substances 0.000 claims description 8
- 229910052793 cadmium Inorganic materials 0.000 claims description 7
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 7
- 229910017052 cobalt Inorganic materials 0.000 claims description 7
- 239000010941 cobalt Substances 0.000 claims description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 claims description 7
- 150000003460 sulfonic acids Chemical class 0.000 claims description 7
- 150000003626 triacylglycerols Chemical class 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052787 antimony Inorganic materials 0.000 claims description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229910052804 chromium Inorganic materials 0.000 claims description 4
- 239000011651 chromium Substances 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 150000003751 zinc Chemical class 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 235000019197 fats Nutrition 0.000 description 50
- 239000003760 tallow Substances 0.000 description 45
- 239000002253 acid Substances 0.000 description 34
- 150000001408 amides Chemical class 0.000 description 20
- 238000007127 saponification reaction Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 11
- 230000035484 reaction time Effects 0.000 description 11
- NMOHFBPSMIYLGY-UHFFFAOYSA-L zinc;2-dodecylbenzenesulfonate Chemical compound [Zn+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O NMOHFBPSMIYLGY-UHFFFAOYSA-L 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
- 235000021588 free fatty acids Nutrition 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 235000015278 beef Nutrition 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 2
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 229910001570 bauxite Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- DUXYWXYOBMKGIN-UHFFFAOYSA-N trimyristin Chemical compound CCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC DUXYWXYOBMKGIN-UHFFFAOYSA-N 0.000 description 2
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- QZHDEAJFRJCDMF-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QZHDEAJFRJCDMF-UHFFFAOYSA-M 0.000 description 1
- UBEIMDKGOYBUKT-FLIQGJDUSA-N 1,2,3-trilinolenoylglycerol Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC UBEIMDKGOYBUKT-FLIQGJDUSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 1
- YRJSLCBKZMMEPB-UHFFFAOYSA-N 2-(2-methylpropyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CC(C)C)=CC=C21 YRJSLCBKZMMEPB-UHFFFAOYSA-N 0.000 description 1
- BMRVLXHIZWDOOK-UHFFFAOYSA-N 2-butylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCC)=CC=C21 BMRVLXHIZWDOOK-UHFFFAOYSA-N 0.000 description 1
- CTIFKKWVNGEOBU-UHFFFAOYSA-N 2-hexadecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O CTIFKKWVNGEOBU-UHFFFAOYSA-N 0.000 description 1
- AQQPJNOXVZFTGE-UHFFFAOYSA-N 2-octadecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O AQQPJNOXVZFTGE-UHFFFAOYSA-N 0.000 description 1
- ZTFYJIXFKGPCHV-UHFFFAOYSA-N 2-propan-2-ylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C(C)C)=CC=C21 ZTFYJIXFKGPCHV-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DSEKYWAQQVUQTP-UHFFFAOYSA-N Cerin Natural products CC12CCC3(C)C4CC(C)(C)CCC4(C)CCC3(C)C2CCC2(C)C1CC(O)C(=O)C2C DSEKYWAQQVUQTP-UHFFFAOYSA-N 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
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- 240000004244 Cucurbita moschata Species 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
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- 239000005662 Paraffin oil Substances 0.000 description 1
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- 241001494479 Pecora Species 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003568 Sodium, potassium and calcium salts of fatty acids Substances 0.000 description 1
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 1
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- 244000098338 Triticum aestivum Species 0.000 description 1
- DVMAOYMRSDRCFX-UHFFFAOYSA-N [Co].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 Chemical compound [Co].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 DVMAOYMRSDRCFX-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
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- 210000000988 bone and bone Anatomy 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- AFEGBMDYBRZHOY-UHFFFAOYSA-N cadmium;dodecyl benzenesulfonate Chemical compound [Cd].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 AFEGBMDYBRZHOY-UHFFFAOYSA-N 0.000 description 1
- 235000013969 calcium salts of fatty acid Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
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- 238000011437 continuous method Methods 0.000 description 1
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- 239000002285 corn oil Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- FGPZBVIFLOFHFM-UHFFFAOYSA-N dodecyl benzenesulfonate;iron Chemical compound [Fe].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 FGPZBVIFLOFHFM-UHFFFAOYSA-N 0.000 description 1
- RPXYMVMDOAUFGX-UHFFFAOYSA-N dodecyl benzenesulfonate;zinc Chemical compound [Zn].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 RPXYMVMDOAUFGX-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 150000002196 fatty nitriles Chemical class 0.000 description 1
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- 238000011010 flushing procedure Methods 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
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- CACRRXGTWZXOAU-UHFFFAOYSA-N octadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCCCCS(O)(=O)=O CACRRXGTWZXOAU-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
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- FODHIQQNHOPUKH-UHFFFAOYSA-N tetrapropylene-benzenesulfonic acid Chemical compound CC1CC11C2=C3S(=O)(=O)OC(C)CC3=C3C(C)CC3=C2C1C FODHIQQNHOPUKH-UHFFFAOYSA-N 0.000 description 1
- ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
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- PHYFQTYBJUILEZ-WUOFIQDXSA-N trielaidin Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C\CCCCCCCC)COC(=O)CCCCCCC\C=C\CCCCCCCC PHYFQTYBJUILEZ-WUOFIQDXSA-N 0.000 description 1
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N trilaurin Chemical compound CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
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- 229960001947 tripalmitin Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- JLVUSDMLNQQPCD-UHFFFAOYSA-L zinc;phenylmethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)CC1=CC=CC=C1.[O-]S(=O)(=O)CC1=CC=CC=C1 JLVUSDMLNQQPCD-UHFFFAOYSA-L 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/22—Preparation of carboxylic acid nitriles by reaction of ammonia with carboxylic acids with replacement of carboxyl groups by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/22—Trihydroxylic alcohols, e.g. glycerol
- C07C31/225—Glycerol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772737607 DE2737607A1 (de) | 1977-08-20 | 1977-08-20 | Verfahren zur herstellung von fettsaeurenitrilen und glycerin aus glyceriden, insbesondere aus natuerlichen fetten und oelen |
| DE19782813204 DE2813204A1 (de) | 1978-03-25 | 1978-03-25 | Verfahren zur herstellung von fettsaeurennitrilen und glycerin aus glyceriden, insbesondere aus natuerlichen fetten und oelen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL209133A1 PL209133A1 (pl) | 1979-05-07 |
| PL119196B1 true PL119196B1 (en) | 1981-12-31 |
Family
ID=25772581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1978209133A PL119196B1 (en) | 1977-08-20 | 1978-08-19 | Method of manufacture of nitriles of fatty acids and glycerol from glycenides,especially from natural fats and oilsiz gliceridov,glavnym obrazom iz natural'nykh zhirov i masel |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US4234509A (fr) |
| EP (1) | EP0000916B1 (fr) |
| JP (1) | JPS5441806A (fr) |
| AR (1) | AR218080A1 (fr) |
| AT (1) | AT359991B (fr) |
| AU (1) | AU519437B2 (fr) |
| BG (1) | BG33734A3 (fr) |
| BR (1) | BR7805331A (fr) |
| CA (1) | CA1135722A (fr) |
| CS (1) | CS202509B2 (fr) |
| DD (1) | DD138311A5 (fr) |
| DE (1) | DE2860715D1 (fr) |
| DK (1) | DK159064C (fr) |
| EG (1) | EG13422A (fr) |
| ES (1) | ES472553A1 (fr) |
| FI (1) | FI63961C (fr) |
| GR (1) | GR73064B (fr) |
| HK (1) | HK8184A (fr) |
| HU (1) | HU180472B (fr) |
| IE (1) | IE47316B1 (fr) |
| IL (1) | IL55385A (fr) |
| IN (1) | IN150312B (fr) |
| IT (1) | IT1099021B (fr) |
| MX (1) | MX147995A (fr) |
| MY (1) | MY8500553A (fr) |
| NO (1) | NO147271C (fr) |
| NZ (1) | NZ188179A (fr) |
| OA (1) | OA06038A (fr) |
| PH (1) | PH16609A (fr) |
| PL (1) | PL119196B1 (fr) |
| PT (1) | PT68440A (fr) |
| RO (1) | RO77028A (fr) |
| SG (1) | SG37883G (fr) |
| SU (1) | SU971092A3 (fr) |
| TR (1) | TR20021A (fr) |
| YU (1) | YU197778A (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3131968A1 (de) * | 1981-08-13 | 1983-02-24 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von aliphatischen nitrilen |
| EP0224706A1 (fr) * | 1985-11-01 | 1987-06-10 | F. Hoffmann-La Roche Ag | Procédé pour la préparation d'un oxazole |
| DE3639857A1 (de) * | 1986-11-21 | 1988-06-01 | Hoechst Ag | Verfahren zur herstellung von fettsaeurenitrilen und glycerin aus glyceriden |
| US6063369A (en) * | 1998-03-16 | 2000-05-16 | Alterna, Inc. | Quaternized hemp seed oil |
| JP4972387B2 (ja) * | 2006-03-08 | 2012-07-11 | 花王株式会社 | 脂肪族ニトリルの製造方法 |
| EP1999105A1 (fr) * | 2006-03-08 | 2008-12-10 | Kao Corporation | Procede de production de nitriles aliphatiques |
| FR2907781B1 (fr) * | 2006-10-27 | 2010-01-08 | Ceca Sa | Procede de synthese de diamines et/ou de triamines primaires de haute purete a partir d'acides dimeres ou trimeres |
| FR2916445B1 (fr) * | 2007-05-24 | 2009-07-10 | Arkema France | Procede de co-production de carbonates cycliques et de nitriles et/ou d'amines gras |
| GT200700043A (es) * | 2007-05-25 | 2008-03-03 | Biocompuestos de funcion nitrilo | |
| CN102844354B (zh) | 2010-02-18 | 2015-07-08 | 巴斯夫欧洲公司 | 含有具有不饱和脂肪酸基团的高支化聚碳酸酯的聚合物分散体 |
| WO2016188830A1 (fr) | 2015-05-22 | 2016-12-01 | Akzo Nobel Chemicals International B.V. | Solvants à base de nitriles gras pour formulations agricoles |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2037389A (en) * | 1932-02-03 | 1936-04-14 | Ig Farbenindustrie Ag | Nitriles of higher unsaturated fatty acids and a process of preparing them |
| GB416631A (en) * | 1934-02-01 | 1934-09-18 | Ig Farbenindustrie Ag | Manufacture of nitriles of unsaturated fatty acids |
| GB451594A (en) * | 1935-02-05 | 1936-08-05 | Ig Farbenindustrie Ag | Improvements relating to the production of nitriles |
| GB477463A (en) * | 1935-12-09 | 1937-12-30 | Armour & Co | Improvements in process of preparing nitriles |
| FR864571A (fr) * | 1939-06-02 | 1941-04-30 | Rhone Poulenc Sa | Procédé de préparation de l'adiponitrile |
| DK78377C (da) * | 1940-10-05 | 1954-11-08 | Armour & Co | Fremgangsmåde til fremstilling af nitriler af mættede eller umættede fedtsyrer. |
| US2524831A (en) * | 1945-10-17 | 1950-10-10 | Armour & Co | Manufacture of nitriles |
| US2493637A (en) * | 1948-05-01 | 1950-01-03 | Rohm & Haas | Process for the preparation of aliphatic nitriles |
| US2589232A (en) * | 1950-03-14 | 1952-03-18 | Hercules Powder Co Ltd | Method of preparing stabilized fatty acid nitriles |
| US2794043A (en) * | 1955-01-13 | 1957-05-28 | Goodrich Co B F | Preparation of aliphatic nitriles |
| US2808426A (en) * | 1956-01-26 | 1957-10-01 | Armour & Co | Preparation of nitriles |
| US2993926A (en) * | 1957-10-30 | 1961-07-25 | Archer Daniels Midland Co | Method of preparing nitriles |
| CH494210A (de) * | 1968-03-27 | 1970-07-31 | Sandoz Ag | Verfahren zur Herstellung von Nitrilen |
| US3850974A (en) * | 1973-05-23 | 1974-11-26 | Akzona Inc | Production of nitriles |
-
1978
- 1978-08-14 IN IN889/CAL/78A patent/IN150312B/en unknown
- 1978-08-14 ES ES472553A patent/ES472553A1/es not_active Expired
- 1978-08-15 BG BG7840672A patent/BG33734A3/xx unknown
- 1978-08-15 RO RO197894982A patent/RO77028A/fr unknown
- 1978-08-16 DD DD78207321A patent/DD138311A5/xx not_active IP Right Cessation
- 1978-08-16 EP EP78100666A patent/EP0000916B1/fr not_active Expired
- 1978-08-16 EG EG511/78A patent/EG13422A/xx active
- 1978-08-16 DE DE7878100666T patent/DE2860715D1/de not_active Expired
- 1978-08-17 JP JP9957878A patent/JPS5441806A/ja active Granted
- 1978-08-17 FI FI782516A patent/FI63961C/fi not_active IP Right Cessation
- 1978-08-17 YU YU01977/78A patent/YU197778A/xx unknown
- 1978-08-18 PH PH21508A patent/PH16609A/en unknown
- 1978-08-18 MX MX174574A patent/MX147995A/es unknown
- 1978-08-18 NO NO782821A patent/NO147271C/no unknown
- 1978-08-18 CS CS785425A patent/CS202509B2/cs unknown
- 1978-08-18 AR AR273352A patent/AR218080A1/es active
- 1978-08-18 AU AU39076/78A patent/AU519437B2/en not_active Expired
- 1978-08-18 IT IT26849/78A patent/IT1099021B/it active
- 1978-08-18 IE IE1677/78A patent/IE47316B1/en unknown
- 1978-08-18 OA OA56581A patent/OA06038A/fr unknown
- 1978-08-18 BR BR7805331A patent/BR7805331A/pt unknown
- 1978-08-18 PT PT68440A patent/PT68440A/pt unknown
- 1978-08-18 HU HU78HO2097A patent/HU180472B/hu unknown
- 1978-08-18 GR GR57029A patent/GR73064B/el unknown
- 1978-08-18 DK DK367978A patent/DK159064C/da not_active IP Right Cessation
- 1978-08-18 CA CA000309619A patent/CA1135722A/fr not_active Expired
- 1978-08-18 NZ NZ188179A patent/NZ188179A/xx unknown
- 1978-08-18 IL IL55385A patent/IL55385A/xx unknown
- 1978-08-18 SU SU782650552A patent/SU971092A3/ru active
- 1978-08-18 AT AT600778A patent/AT359991B/de not_active IP Right Cessation
- 1978-08-19 PL PL1978209133A patent/PL119196B1/pl unknown
-
1979
- 1979-04-24 US US06/032,753 patent/US4234509A/en not_active Expired - Lifetime
-
1980
- 1980-05-23 TR TR20021A patent/TR20021A/xx unknown
-
1983
- 1983-06-30 SG SG378/83A patent/SG37883G/en unknown
-
1984
- 1984-02-01 HK HK81/84A patent/HK8184A/xx unknown
-
1985
- 1985-12-30 MY MY553/85A patent/MY8500553A/xx unknown
Also Published As
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